US4309183A - Liquid crystal phase of an azo reactive dyestuff and its use for dyeing and printing natural and synthetic substrates - Google Patents
Liquid crystal phase of an azo reactive dyestuff and its use for dyeing and printing natural and synthetic substrates Download PDFInfo
- Publication number
- US4309183A US4309183A US06/208,592 US20859280A US4309183A US 4309183 A US4309183 A US 4309183A US 20859280 A US20859280 A US 20859280A US 4309183 A US4309183 A US 4309183A
- Authority
- US
- United States
- Prior art keywords
- liquid crystal
- dyeing
- crystal phase
- dyestuff
- synthetic substrates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 title claims abstract description 10
- 238000004043 dyeing Methods 0.000 title claims abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 title description 7
- 239000000758 substrate Substances 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004976 Lyotropic liquid crystal Substances 0.000 claims abstract description 5
- 239000004627 regenerated cellulose Substances 0.000 claims abstract description 4
- 229920000742 Cotton Polymers 0.000 claims abstract description 3
- 239000010985 leather Substances 0.000 claims abstract description 3
- 239000000123 paper Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 210000002268 wool Anatomy 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 4
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 239000008346 aqueous phase Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000002535 lyotropic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001988 small-angle X-ray diffraction Methods 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
- C09B62/40—Azo dyes
- C09B62/405—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/919—Paper
Definitions
- the invention relates to the lyotropic liquid crystal aqueous phase of the dyestuff of the formula ##STR2## present in water in a concentration of 12-35% at room temperature, and the use of these lyotropic liquid crystals for the preparation of dyebaths and printing pastes for dyeing and/or printing natural and synthetic substrates, in particular cotton, wool, regenerated cellulose, paper and leather.
- This phase exhibits the birefringence and formation of a structured diffraction pattern on small-angle X-ray diffraction which are characteristic of liquid crystals.
- lyotropic liquid crystals are characterised in the customary manner by the interference colours formed, as a result of birefringence, when these liquid crystals are inserted between crossed nicols in a polarisation microscope, and/or by the structured diffraction pattern on small-angle X-ray diffraction with Cu-K ⁇ -radiation in a Kie ⁇ ig chamber (compare, for example, G. H. Brown: Flussige Kristalle (Liquid Crystals); Chem. uns. Zeit, 2, 1968, pages 43-51 and Eckert and Kramer: Pharmazie uns. Zeit 1, 1972 (116-121)).
- liquid crystal phase is also retained when small amounts of inorganic salts, in particular sodium chloride, sodium sulphate or sodium acetate, or customary buffer mixtures and/or water-miscible organic solvents, such as alcohols, polyols, ethers or esters thereof or amides, and/or hydrotropic substances, such as urea, are added.
- inorganic salts in particular sodium chloride, sodium sulphate or sodium acetate, or customary buffer mixtures and/or water-miscible organic solvents, such as alcohols, polyols, ethers or esters thereof or amides, and/or hydrotropic substances, such as urea
- the physical form, according to the invention, of the dyestuff is obtained when the almost salt-free dyestuff of the formula I is liquefied with water within the abovementioned concentration range.
- the new physical form can also be obtained directly if the aqueous solution or mixture which is obtained by the customary synthesis and has a high salt content is subjected to pressure permeation.
- the new physical form, according to the invention, of the dyestuff is a liquid finished formulation which is exceptionally stable to storage and hydrolysis.
- a highly concentrated, lyotropic liquid crystal phase which is stable to storage and hydrolysis and which exhibits characteristic interference colours when inserted between crossed nicols in a polarisation microscope is obtained.
- this phase is stirred into water and thickeners and the auxiliaries customary in the dyeing industry are added, a printing paste which can be used for printing natural and regenerated cellulose fibers in reddish-tinged yellow shades is obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Liquid finished formulations which are stable to storage and hydrolysis and are based on the lyotropic liquid crystal aqueous phase of the dyestuff of the formula ##STR1## in water in a concentration of 12-35% at room temperature are outstandingly suitable for the preparation of dyebaths and printing pastes for dyeing cotton, wool, regenerated cellulose, paper and leather.
Description
The invention relates to the lyotropic liquid crystal aqueous phase of the dyestuff of the formula ##STR2## present in water in a concentration of 12-35% at room temperature, and the use of these lyotropic liquid crystals for the preparation of dyebaths and printing pastes for dyeing and/or printing natural and synthetic substrates, in particular cotton, wool, regenerated cellulose, paper and leather.
This phase exhibits the birefringence and formation of a structured diffraction pattern on small-angle X-ray diffraction which are characteristic of liquid crystals.
These lyotropic liquid crystals are characterised in the customary manner by the interference colours formed, as a result of birefringence, when these liquid crystals are inserted between crossed nicols in a polarisation microscope, and/or by the structured diffraction pattern on small-angle X-ray diffraction with Cu-Kα-radiation in a Kieβig chamber (compare, for example, G. H. Brown: Flussige Kristalle (Liquid Crystals); Chem. uns. Zeit, 2, 1968, pages 43-51 and Eckert and Kramer: Pharmazie uns. Zeit 1, 1972 (116-121)).
The liquid crystal phase is also retained when small amounts of inorganic salts, in particular sodium chloride, sodium sulphate or sodium acetate, or customary buffer mixtures and/or water-miscible organic solvents, such as alcohols, polyols, ethers or esters thereof or amides, and/or hydrotropic substances, such as urea, are added.
The physical form, according to the invention, of the dyestuff, is obtained when the almost salt-free dyestuff of the formula I is liquefied with water within the abovementioned concentration range. The new physical form can also be obtained directly if the aqueous solution or mixture which is obtained by the customary synthesis and has a high salt content is subjected to pressure permeation.
The new physical form, according to the invention, of the dyestuff is a liquid finished formulation which is exceptionally stable to storage and hydrolysis.
20 g of the completely salt-free or almost salt-free dyestuff of the formula I are liquefied with 80 g of water at room temperature in the course of several hours, whilst stirring.
A highly concentrated, lyotropic liquid crystal phase which is stable to storage and hydrolysis and which exhibits characteristic interference colours when inserted between crossed nicols in a polarisation microscope is obtained. When this phase is stirred into water and thickeners and the auxiliaries customary in the dyeing industry are added, a printing paste which can be used for printing natural and regenerated cellulose fibers in reddish-tinged yellow shades is obtained.
Claims (2)
1. Lyotropic liquid crystal phase of the dyestuff of the formula ##STR3## present in water in a concentration of 12-35% at room temperature.
2. A method for the preparation of dyebaths and printing pastes for dyeing and/or printing cotton, wool, regenerated cellulose, paper or leather which comprises using, as the dyestuff, the lyotropic liquid crystal phase of the dyestuff of claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2948291 | 1979-11-30 | ||
| DE19792948291 DE2948291A1 (en) | 1979-11-30 | 1979-11-30 | LIQUID CRYSTAL PHASE OF AN AZOREACTIVE DYE AND THE USE THEREOF FOR COLORING AND PRINTING NATURAL AND SYNTHETIC SUBSTRATES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4309183A true US4309183A (en) | 1982-01-05 |
Family
ID=6087304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/208,592 Expired - Lifetime US4309183A (en) | 1979-11-30 | 1980-11-19 | Liquid crystal phase of an azo reactive dyestuff and its use for dyeing and printing natural and synthetic substrates |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4309183A (en) |
| EP (1) | EP0029959B1 (en) |
| JP (1) | JPS5686960A (en) |
| BR (1) | BR8007797A (en) |
| DE (2) | DE2948291A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443225A (en) * | 1981-12-11 | 1984-04-17 | Bayer Aktiengesellschaft | Liquid-crystalline phase of an azo reactive dyestuff, and its use for the dyeing and printing of natural and synthetic substrates |
| US5001173A (en) * | 1987-05-11 | 1991-03-19 | Morton Coatings, Inc. | Aqueous epoxy resin compositions and metal substrates coated therewith |
| US6180295B1 (en) | 1998-09-11 | 2001-01-30 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
| US6214499B1 (en) | 1998-09-11 | 2001-04-10 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
| US6245255B1 (en) | 1998-09-11 | 2001-06-12 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666747A (en) * | 1968-11-13 | 1972-05-30 | Bayer Ag | Azo dyestuffs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191059B (en) * | 1961-02-07 | 1965-04-15 | Bayer Ag | Process for the production of azo dyes |
| IT949703B (en) * | 1971-02-02 | 1973-06-11 | Ciba Geigy Ag | PROCEDURE FOR PRODUCING THE PREPARATION OF CONCENTRATED LIQUID COLORINGS LOW IN SALTS |
-
1979
- 1979-11-30 DE DE19792948291 patent/DE2948291A1/en not_active Withdrawn
-
1980
- 1980-11-19 EP EP80107191A patent/EP0029959B1/en not_active Expired
- 1980-11-19 US US06/208,592 patent/US4309183A/en not_active Expired - Lifetime
- 1980-11-19 DE DE8080107191T patent/DE3065394D1/en not_active Expired
- 1980-11-27 JP JP16596080A patent/JPS5686960A/en active Pending
- 1980-11-28 BR BR8007797A patent/BR8007797A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666747A (en) * | 1968-11-13 | 1972-05-30 | Bayer Ag | Azo dyestuffs |
Non-Patent Citations (2)
| Title |
|---|
| Hackh's Chemical Dictionary, Fourth Edition, (McGraw-Hil), 1972, p. 399. * |
| John Griffiths' "Colour and Constitution of Organic Molecules" (Academic Press) 1976, p. 71. * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443225A (en) * | 1981-12-11 | 1984-04-17 | Bayer Aktiengesellschaft | Liquid-crystalline phase of an azo reactive dyestuff, and its use for the dyeing and printing of natural and synthetic substrates |
| US5001173A (en) * | 1987-05-11 | 1991-03-19 | Morton Coatings, Inc. | Aqueous epoxy resin compositions and metal substrates coated therewith |
| US6180295B1 (en) | 1998-09-11 | 2001-01-30 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
| US6214499B1 (en) | 1998-09-11 | 2001-04-10 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
| US6245255B1 (en) | 1998-09-11 | 2001-06-12 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
| US6355386B1 (en) * | 1998-09-11 | 2002-03-12 | Eastman Kodak Company | Liquid crystalline filter dyes for imaging elements |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0029959A3 (en) | 1982-05-05 |
| BR8007797A (en) | 1981-06-16 |
| DE2948291A1 (en) | 1981-06-04 |
| JPS5686960A (en) | 1981-07-15 |
| EP0029959A2 (en) | 1981-06-10 |
| DE3065394D1 (en) | 1983-11-24 |
| EP0029959B1 (en) | 1983-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |